Trupanion COO exercises RSUs, covers tax with shares

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Form Type

Rhea-AI Filing Summary

TRUPANION, INC. Chief Operating Officer John R. Gallagher reported routine equity compensation activity involving restricted stock units that vested and converted into common stock. On February 25, 2026, RSUs converted into common shares on a one-for-one basis at no exercise price.

Gallagher acquired common stock through derivative exercises and had a portion of the newly vested shares withheld by the company to cover income tax obligations at a price of $26.70 per share, which the footnotes clarify does not represent an open-market sale. After these transactions, he directly held 37,670 shares of common stock.

Insider Trade Summary

1,260 shares exercised/converted

Exercise 12 txns

Insider GALLAGHER JOHN R

Role Chief Operating Officer

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Unit (RSU)	735	$0.00	$0.00
Exercise	Restricted Stock Unit (RSU)	29	$0.00	$0.00
Exercise	Restricted Stock Unit (RSU)	451	$0.00	$0.00
Exercise	Restricted Stock Unit (RSU)	45	$0.00	$0.00
Exercise	Common Stock	735	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	178	$26.70	$5K
Exercise	Common Stock	29	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	7	$26.70	$186.90
Exercise	Common Stock	451	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	109	$26.70	$3K
Exercise	Common Stock	45	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	10	$26.70	$267.00

Holdings After Transaction: Restricted Stock Unit (RSU) — 3,123 contracts (Direct); Common Stock — 37,670 shares (Direct)

Footnotes (7)

F1. Restricted stock units convert into common stock on a one-for-one basis.
F2. This Form 4 discloses the shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations in connection with the vesting of the restricted stock units, and does not represent a sale by the reporting person.
F3. On February 28, 2022, the reporting person was granted 11,752 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F4. The RSUs convert into common stock on a one-for-one basis.
F5. On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F6. On August 14, 2023, the reporting person was granted 7,223 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.
F7. On August 14, 2023, the reporting person was granted 721 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transactions did TRUP COO John R. Gallagher report?

John R. Gallagher reported RSU vesting that converted into common stock and related share withholdings for taxes. The activity reflects equity compensation mechanics, with RSUs settling one-for-one into Trupanion common shares rather than discretionary market purchases or sales.

How many Trupanion (TRUP) shares did the COO acquire from RSU vesting?

The COO acquired common stock through several RSU conversions, with the derivative entries showing restricted stock units converting into common shares at a zero exercise price. Each restricted stock unit converts into one share of Trupanion common stock under the grant terms described in the footnotes.

Why were some TRUP shares disposed of in John R. Gallagher’s Form 4?

Shares marked as dispositions were withheld by Trupanion to satisfy income tax withholding and remittance obligations tied to RSU vesting. A footnote states this withholding does not represent a sale by Gallagher, distinguishing it from open-market selling activity.

What price was used for Trupanion shares withheld for taxes on the RSUs?

Shares withheld to cover taxes were valued at $26.70 per share in multiple tax-withholding disposition entries. This price is used solely for satisfying tax obligations associated with RSU vesting rather than indicating a negotiated market transaction by the executive.

How many Trupanion (TRUP) shares does the COO own after these transactions?

Following the RSU conversions and tax-related share withholdings reported on February 25, 2026, John R. Gallagher directly owned 37,670 shares of Trupanion common stock. This figure reflects his updated direct holdings after all listed derivative and non-derivative transactions.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 02/27/2026 - 08:02 PM EST

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

GALLAGHER JOHN R

(Last)

(First)

(Middle)

6100 4TH AVENUE S

SUITE 200

(Street)

SEATTLE

98108

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
TRUPANION, INC. [ TRUP ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Operating Officer

3. Date of Earliest Transaction (Month/Day/Year)
02/25/2026

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	02/25/2026		M		735	A	⁽¹⁾	37,449	D
Common Stock	02/25/2026		F		178⁽²⁾	D	$26.7	37,271	D
Common Stock	02/25/2026		M		29	A	⁽¹⁾	37,300	D
Common Stock	02/25/2026		F		7⁽²⁾	D	$26.7	37,293	D
Common Stock	02/25/2026		M		451	A	⁽¹⁾	37,744	D
Common Stock	02/25/2026		F		109⁽²⁾	D	$26.7	37,635	D
Common Stock	02/25/2026		M		45	A	⁽¹⁾	37,680	D
Common Stock	02/25/2026		F		10⁽²⁾	D	$26.7	37,670	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Unit (RSU)	⁽¹⁾	02/25/2026		M			735	⁽³⁾	02/25/2026⁽³⁾	Common Stock	735	$0	0	D
Restricted Stock Unit (RSU)	⁽⁴⁾	02/25/2026		M			29	⁽⁵⁾	05/25/2027⁽⁵⁾	Common Stock	29	$0	144	D
Restricted Stock Unit (RSU)	⁽¹⁾	02/25/2026		M			451	⁽⁶⁾	08/25/2027⁽⁶⁾	Common Stock	451	$0	2,709	D
Restricted Stock Unit (RSU)	⁽¹⁾	02/25/2026		M			45	⁽⁷⁾	08/25/2027⁽⁷⁾	Common Stock	45	$0	270	D

Explanation of Responses:

1. Restricted stock units convert into common stock on a one-for-one basis.

2. This Form 4 discloses the shares of common stock that have been withheld by the issuer to satisfy its income tax withholding and remittance obligations in connection with the vesting of the restricted stock units, and does not represent a sale by the reporting person.

3. On February 28, 2022, the reporting person was granted 11,752 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on February 25, 2023, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

4. The RSUs convert into common stock on a one-for-one basis.

5. On May 15, 2023, the reporting person was granted 460 restricted stock units (RSUs). The RSUs vested and converted into common stock of the Issuer as to 1/4th of the total shares on May 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

6. On August 14, 2023, the reporting person was granted 7,223 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

7. On August 14, 2023, the reporting person was granted 721 restricted stock units (RSUs). The RSUs vest and convert into common stock of the Issuer as to 1/4th of the total shares on August 25, 2024, after which 1/16th of the total shares vest quarterly, subject to continued service through each vest date.

Remarks:

	/s/ Lauren Welsh as attorney-in-fact for John R. Gallagher	02/27/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

Source: View Original Filing on SEC EDGAR